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ChemInform Abstract: Conformational Bias by a Removable Substituent. Synthesis of Eight- Membered Cyclic Ethers via Ring-Closing Metathesis.

✍ Scribed by R. J. LINDERMAN; J. SIEDLECKI; S. A. O'NEILL; H. SUN

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199741210

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✦ Synopsis

Conformational Bias by a Removable Substituent.

Synthesis of Eight-Membered Cyclic Ethers via Ring-Closing Metathesis.

-Ru-catalyzed ring-closing metathesis of acyclic α-(alkoxyalkyl)-stannylsubstituted dienes leads to the synthesis of six-, seven-, and eight-membered α-trialkylstannyl-substituted cyclic ethers in good yields. Corresponding reactions with analogous compounds carrying a tBu-group instead of a SnBu3-group lead to different results, thus the SnBu3 group favors intramolecular cyclization over polymerization in the metathesis reaction compared to the tBu-substituent.

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